Vapochromic and semiconducting solids of a bifunctional hydrocarbon

Xia, Hai Long; Liu, Danqing; Song, Kang; Miao, Qian

doi:10.1039/c1sc00494h

Cited by 31 publications

(28 citation statements)

References 47 publications

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“…Unlike five-membered rings, seven-membered rings can give rise to saddle-shaped p-molecules with negative curvature [6] and stabilize holes injected into p-type organic semiconductors by forming the aromatic cycloheptatrienyl cation. [7] However, conjugated polycyclic hydrocarbons containing seven-membered rings have been rarely explored. Herein, we report dibenzo [d,d']benzo [1,2-a:4,5-a']dicycloheptene derivatives (1 a-c, Figure 1), [8] which have an unprecedented pentacyclic conjugated backbone containing two seven-membered carbocycles.…”

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confidence: 99%

Heptagon‐Embedded Pentacene: Synthesis, Structures, and Thin‐Film Transistors of Dibenzo[d,d′]benzo[1,2‐a:4,5‐a′]dicycloheptenes

2014

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This study presents a new class of conjugated polycyclic molecules that contain seven-membered rings, detailing their synthesis, crystal structures and semiconductor properties. These molecules have a nearly flat C6-C7-C6-C7-C6 polycyclic framework with a p-quinodimethane core. With field-effect mobilities of up to 0.76 cm(2) V(-1) s(-1) as measured from solution-processed thin-film transistors, these molecules are alternatives to the well-studied pentacene analogues for applications in organic electronic devices.

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confidence: 99%

Heptagon‐Embedded Pentacene: Synthesis, Structures, and Thin‐Film Transistors of Dibenzo[d,d′]benzo[1,2‐a:4,5‐a′]dicycloheptenes

2014

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“…Close inspection of the interaction of the extended π‐conjugated pyrene‐based helicene reveals that neighboring molecules of 7 b interact with each other in both face‐to face and edge‐to‐face modes . The unit cell of this crystal contains three pairs of enantiomers of 7 b together with crystallized solvent molecules as shown in Figure b.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Structure and Photophysical Properties of Pyrene–based [5]Helicenes: an Experimental and Theoretical Study

et al. 2017

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International audiencePyrene-cored [5]helicenes were prepared by a facile, efficient Wittig reaction and an intramolecular photocyclization reaction utilising 2,7-di-tert-butylpyrene-4-carbaldehyde and naphthalene/pyrene-based phosphorus ylides. Optical properties based on UV À vis absorption and fluorescence spectra were investigated. X-ray crystallography revealed that the pyrene-based [5]helicenes exhibited strong face-to-face p À p interactions and edge-to-face p À p interactions. HOMO and LUMO energies and molecular orbitals were also studied by density functional theory (DFT) calculations. This study has revealed that the torsion angle of the helical structure plays a role in determining the p À p interactions and the frontier molecular orbital energy levels. Thus, pyrene-based helicenes need to be considered when one designs new highly efficient organic light-emitting diodes and organic semiconductor materials

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“…This group of molecules include curved π‐conjugated molecules known as aromatic bowls2, 3 (or buckybowls4) and electron acceptors5 as applied in organic electronics, since the five‐membered rings can not only introduce positive curvature but also stabilize injected electrons by forming the aromatic cyclopentadienyl anion. Unlike five‐membered rings, seven‐membered rings can give rise to saddle‐shaped π‐molecules with negative curvature6 and stabilize holes injected into p‐type organic semiconductors by forming the aromatic cycloheptatrienyl cation 7. However, conjugated polycyclic hydrocarbons containing seven‐membered rings have been rarely explored.…”

Section: Methodsmentioning

confidence: 99%

Heptagon‐Embedded Pentacene: Synthesis, Structures, and Thin‐Film Transistors of Dibenzo[d,d′]benzo[1,2‐a:4,5‐a′]dicycloheptenes

2014

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This study presents a new class of conjugated polycyclic molecules that contain seven-membered rings, detailing their synthesis, crystal structures and semiconductor properties. These molecules have a nearly flat C 6 -C 7 -C 6 -C 7 -C 6 polycyclic framework with a p-quinodimethane core. With field-effect mobilities of up to 0.76 cm 2 V À1 s À1 as measured from solution-processed thin-film transistors, these molecules are alternatives to the well-studied pentacene analogues for applications in organic electronic devices.

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Vapochromic and semiconducting solids of a bifunctional hydrocarbon

Cited by 31 publications

References 47 publications

Heptagon‐Embedded Pentacene: Synthesis, Structures, and Thin‐Film Transistors of Dibenzo[d,d′]benzo[1,2‐a:4,5‐a′]dicycloheptenes

Heptagon‐Embedded Pentacene: Synthesis, Structures, and Thin‐Film Transistors of Dibenzo[d,d′]benzo[1,2‐a:4,5‐a′]dicycloheptenes

Synthesis, Structure and Photophysical Properties of Pyrene–based [5]Helicenes: an Experimental and Theoretical Study

Heptagon‐Embedded Pentacene: Synthesis, Structures, and Thin‐Film Transistors of Dibenzo[d,d′]benzo[1,2‐a:4,5‐a′]dicycloheptenes

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